


Assistant to the CEO

by NavajoLovesDestiel



Series: SPN Kink Bingo [9]
Category: Supernatural
Genre: Alternate Universe, Anal Sex, Bottom Dean, M/M, Office Sex, Supernatural Kink Bingo 2018, Top Castiel
Language: English
Status: Completed
Published: 2018-06-04
Updated: 2018-06-04
Packaged: 2019-05-18 04:47:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,138
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14846027
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/NavajoLovesDestiel
Summary: He was dressed like someone straight out of GQ. His suit was impeccable, his shoes shined like glass. But what struck Cas straight between his eyes was just how fucking gorgeous Dean Winchester was. All the photos of him certainly didn’t do him justice.





	Assistant to the CEO

**Author's Note:**

> One shot for SPN Kink Bingo  
> square is Office Sex

It was Cas’ first day and he was so nervous he felt like he could throw up. Being the personal assistant to the CEO was his dream, but now that he actually had the job, he felt like he didn’t know if he could do it. He’d never actually met the CEO yet, either, and that was adding to his nerves.

He’d arrived early, just to make sure that everything was exactly like the last assistant had explained Mr. Winchester liked it. She was getting married and quit. Cas was happy that she was going on to a happy life, and really happy he was chosen as her replacement.

He looked up and there the man was. He strode into the place like a force of nature. He stood tall, held his head up and nodded to everyone he passed.

He was dressed like someone straight out of GQ. His suit was impeccable, his shoes shined like glass. But what struck Cas straight between his eyes was just how fucking  _ gorgeous _ Dean Winchester was. All the photos of him certainly didn’t do him justice.

He was walking up to Cas and Cas felt like he was going to pass out. 

Dean stared at him for a moment, his beautiful green eyes flashed amusement. He looked Cas up and down like he was a buffet and Dean was hungry. Starving.

“You must be Cas Novak, my new assistant.” It wasn’t a question, but still, Cas felt like he needed to answer.

“Ye-yes, Sir. I’m very happy to meet you…” Cas trailed off and cursed himself for an idiot.

Dean just smiled. “Well, let’s get to know one another, shall we?” He opened the door to his office and stepped aside, sweeping a hand to indicate that Cas should go through it first.

He did, and then stopped, not knowing exactly what to do. Dean walked in, went to his desk and took off his jacket. 

Cas looked at the man’s amazing physique. He had broad shoulders, and what looked like a chest that would be truly a work of art if he didn’t have a shirt on.

Dean looked at the cup of steaming coffee where it sat on his desk, and smiled.

“Looks like Charlie filled you in pretty well.”

He sat down behind his desk and took a sip. “Very nice, Cas. Just how I like it.”

That gave Cas just a little bit of courage, so he walked up to the desk. “I’m glad I did it right, Sir.”

Dean took another sip and sat the cup down. “Sit.”

So Cas sat. He had grabbed his notepad and a pen on his way in, so he sat waiting instructions.

Dean sat back in his chair and looked at Cas. Cas felt like squirming in his chair under his intense gaze.

“So, Cas, tell me about yourself? Married?”

Cas shook his head. “No, not married and not in a relationship.”

Dean smiled. “Okay, good to know. You probably already know I’m single.”

Cas nodded. 

They meshed together like a well-oiled machine from the beginning. Cas seemed to be able to anticipate Dean’s every need and Dean leaned heavily on Cas.

They worked late many times. 

One night, it was getting late. Dean threw the file he was looking at down with a slap.

“Let’s get some dinner.”

Cas went to grab the take-out menus but Dean grabbed them away from him.

“I mean, let’s get out of here. Go to a real restaurant and eat real food. Come on.”

They put on their jackets and walked out to where Dean’s car was parked. Cas was so nervous as he got in, he felt like he’d pass out. But Dean put on some classic rock and they ended up singing along to a song while Dean drove them to his favorite place to eat.

Cas was surprised at where they ended up, It was a little diner slash bar called The Roadhouse. 

“Best burgers I’ve ever ate.” Dean put his hand on the small of Cas’ back as he guided him inside. Cas felt like Dean’s hand was on fire, it was so hot against his back.

They got a booth and Dean called for two beers. When the waitress came to take their order, Dean just said, “Two with everything.”

Cas relaxed and drank some of his beer. 

Dean looked at him with narrowed eyes. “Cas, can I ask you something that is probably wildly inappropriate?”

Cas said, “Go ahead, Dean. You can ask me anything.”

Dean took a deep breath. “Are you gay?”

Cas just stared into those incredible green eyes.

“Yes, I am.”

Dean grinned. “I am too, Cas.”

Cas swallowed the lump that suddenly appeared in his throat.

“O-okay…”

Dean took a swallow of beer. Then he looked back at Cas.

“I’m really attracted to you.”

Cas smiled. “The feeling is mutual, I assure you.”

Dean sighed. “It would be inappropriate for us to knock boots.”

Cas grinned at the phrasing. “I guess it would, yeah.”

Dean ran his fingers over the lip of his bottle. “But I still want to.”

Cas reached over and put his hand over Dean’s. “I do too.”

Dean waved down the waitress. “We’ll take those burgers to go.”

 

They stood naked in front of each other in Dean’s very spacious bedroom. Dean pulled Cas in for a very filthy kiss. 

They fell on the bed, never breaking the kiss. Dean nipped and kissed his way along Cas’ jaw and down his neck. 

Cas let Dean have his way. He was so worked up, he couldn’t think straight. 

When Dean grabbed the lube, Cas took a deep breath. He watched Dean pour some in his hand.

But what Dean did next surprised Cas immensely. 

Dean reached back and began to use his lubed fingers to open himself up. Cas watched and it was the most erotic thing he’d ever seen.

He listened to Dean moan, and then pull his fingers out of himself. He moved up and positioned himself above Cas’ hard, leaking cock.

When he sank down, they both moaned. 

“Fuck, you feel so good, Cas…”

“You feel amazing. I think my cock is in love with you.”

Dean paused. “Just your cock?”

Cas blushed. “No, not just my cock.”

Dean began to ride him again. “That’s good, because I’m kinda in love with you.”

Cas couldn’t believe his ears.

“I-I love you too, Dean. More than I can say.”

“Good… oh  _ fuck _ ! Good to know. We can talk about that later. Right now, I want to ride you until I walk funny tomorrow.”

And he did exactly that.

The next day, they had sex on Dean’s desk. Cas thought Dean looked amazing bent over with his ass in the air and his suit pants around his ankles.

 


End file.
